Dimethylformamide → Methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl ester

HRID 2047584Notes

Reaction equation

[OH:1][C:2]([C:4]([F:15])([F:14])[CH:5]([O:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])[CH2:6][CH3:7])=O.CN(C)C=O.S1C=CC=C1[Cl:26]>>[Cl:26][C:2]([C:4]([F:15])([F:14])[CH:5]([O:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])[CH2:6][CH3:7])=[O:1]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 72992-Chlorothiophene

HCID 584134402,2-Difluoro-3-(methacryloyloxy)pentanoic acid

Product 1

HCID 58352381Methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl esterYield 92%

Conditions

Temperature: 75 °C

Procedure

Into a 3-L vessel with a dropping funnel, added were 420 g (purity 56%, 1.25 mol) of methacrylic acid 1-hydroxycarbonyl-1,1-difluoro-2-butyl ester obtained in Example 1-3 and 7.50 g (0.11 mol/0.01 eq) of dimethylformamide. Then, 452 g (3.79 mol/0.01 eq) of thienyl chloride were dropped into the vessel at room temperature. The resulting solution was heated to 75° C. and stirred for 4 hours. The completion of the reaction was confirmed by 19F NMR. After that, the solution was distillated under a reduced pressure. With this, 255 g of methacrylic acid 1-chlorocarbonyl-1,1-difluoro-2-butyl ester was obtained (yield: 92%, purity: 98%).

Workup

additionInto a 3-L vessel with a dropping funnel, added

Sources & evidence

ORD record: ord-31a13dea8c204cab8af4712fe20c9160
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592540B2

Reaction notes

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